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How did Ron Shapiro successfully negotiate Joe Mauer’s $184 million contract, the fourth largest contract in the history of baseball? He attributes his success with the Minnesota Twins catcher to his careful preparation. A new book, Perfecting Your Pitch: How to Succeed in Business and in Life by Finding Words That Work, outlines the three-step process he developed as a sports agent and lawyer. Wharton management professor Adam M. Grant recently interviewed Shapiro about the process he uses.

An edited transcript of that conversation follows.

Adam Grant: I’m here with Ron Shapiro, a world-class negotiator, sports agent, lawyer and bestselling author. He has written a new book, Perfecting Your Pitch. What led you to write this book?

Shapiro: One thing that people tend to do when they get to those crucial conversations in life, no matter how good they are at what they do, they think they have it all in their head, and they wing it. No matter how advanced they are, winging it leads to them asking, “Why did I say that?” or “Why didn’t I say that?” I wanted to see if I could offer some suggestions, a cure, for the “Why did I say that?” phenomena.

Grant: What are you favorite cures or suggestions?

Shapiro: I’m a person who believes that whether you are negotiating or dealing with other challenges in life, the great leveler is to find a system that helps you solve the problem, assuming it’s a simple system. What I’ve done in the book is to create a simple, systematic approach. I call it the Three Ds: Draft, Devil’s Advocate and Deliver. That system, if properly employed, really increases the success rate in challenging communications to a nearly 90 percent level. That’s really the goal: to help people speak confidently and accomplish their objectives.

Grant: Did you draft a script for this conversation?

Shapiro: I did not draft it for this conversation. Since the book has come out, I’ve been speaking about it constantly. After my initial presentation, people said, “Wow, that was an amazing 20 minutes, and it was also extemporaneous.” They had no idea how well prepared it was. But that’s a good script. This isn’t a movie script. It isn’t the beginning and the end. It’s really knowing what you’re going to say and speaking it confidently. When I go out and speak about the Three Ds and perfecting your pitch, I’m trying to convince people to improve their lives. That’s a negotiation. I want to speak it confidently and effectively. So, I spent a lot of hours preparing to talk about this book.

Grant: Let’s start on the drafting part then. What are your best practices when you actually sit down to draft a conversation?

Shapiro: When you are going to have a challenging communication, it’s either because something’s on the line or because your emotions are so pent up with anger and other feelings, and you want to express them to people. I say, sit down, whether it be at the computer or with a pen if you still use one, and get it all down. Say everything that’s on your mind. Get your emotions out. Get your arguments down. Don’t worry about whether you are ultimately going to say them, but get them out. Drafting is all about making the initial plan, but a plan that’s going to be revised with the second step. By the way, it’s a great way to get the emotions out of the way. Abraham Lincoln didn’t like his generals in the beginning of the Civil War, but he couldn’t fire them either. So, he would write nasty letters and get it all down. He put them in a drawer. He drafted, and by drafting, got the emotion out of the way.

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Grant: I think the devil’s advocacy was my favorite part of the book. How does that work?

Shapiro: I’ve always needed a devil’s advocate to look over my shoulder at what I drafted to say, “This works, this doesn’t work.” I learned this, by the way, in part by reading about John Adams. John Adams wasn’t the greatest personality in the world, but he had one of the world’s great negotiations when he convinced the 13 colonies to become the 13 United States of America in the Second Continental Congress. Quill in hand, he would draft and he would find someone [to act as a devil’s advocate]. That was Abigail Adams. He would give her the draft, and she would tear it up and put it back together. He obviously ultimately made convincing arguments. We got the Declaration of Independence.

I always say to people, “Who is your Abigail Adams?” I had some key Abigail Adams in my life. In my sports negotiation, my partner Michael Maas has always been there looking over my shoulder, making sure I don’t make the wrong move and helping me calibrate the move so it can be effective. That applies to business negotiations. That applies to familial communications. That’s how the devil’s advocacy process works….

Grant: One of the most enjoyable and useful parts of this book is going through all the different examples where you and others have put this process into action. As a sports fan, I especially enjoyed reading about Joe Mauer and how you negotiated that contract. Can you talk to us a little bit about [that]?

Shapiro: Well, I used two negotiations in the first four chapters of the book to demonstrate how they worked, to teach people the Three Ds. One is Joe Mauer’s $184 million contract, the fourth largest contract in the history of baseball a few years ago, the biggest outside of New York. [I explained how] Michael Maas and I would go through this process, how we would meet with the general manager and how I would script it out and give it to Michael. In the book, I actually show the crossouts and what he gave back to me. I would give it back to him. We would go through the drafting process…. After the devil’s advocacy, we deliver the third step — practicing it. Michael would then go from devil’s advocate to deal coach. He would play the general manager. He would interrupt me because this was a big deal, and we had to do it right. He would get me ready for the questions that might arise because although you script for that ultimate ask, you want to make that number — and let’s say the first number we had was $229 million — a convincing and confident number with a rational basis to it. You also have to understand you’re going to have to be somewhat extemporaneous along the way.

We’ve had some interesting challenges in the negotiation world because I’ve represented the so-called “good guys of baseball” — Cal Ripken, Joe Mauer, Kirby Puckett.

Putting the Three Ds together with Joe Mauer was an excellent example, but I paralleled that in the first four chapters with a young lady named Lindsey who we consulted who had a $50,000 employment contract. She wanted to change some of the terms and conditions of her employment. I showed how parallel they really were in applying this process. She was totally unsophisticated and went through the Three Ds and ramped up and took control of her life and had an effective communication as a result of it.

Grant: The delivery part of it is something that a lot of us overlook, the idea of actually practicing. You have helped to resolve a symphony orchestra strike. You have negotiated over a billion dollars of contracts in your career. Do you still practice?

Shapiro: I really do. I say, “Look, let’s play this out before we get to the next room.” I’m never the smartest guy in the room, but I’m going to be the best prepared guy in the room. I’m going to be the most systematic guy in the room. We’ve had some interesting challenges in the negotiation world because I’ve represented the so-called “good guys of baseball” — Cal Ripken, Joe Mauer, Kirby Puckett. These are guys who didn’t go to the free agent market and yet got record-breaking contracts. How do you do that without the threat?…

It was a tough negotiation, and my goal was not to go in there and be aggressive. My goal was to go in there and be successful….

Grant: Do you do a lot of coaching and consulting on this process?

Shapiro: I say that my favorite career in life is my present career. It wasn’t as a sports agent or as an attorney, it’s as a change agent. A young man from Africa wrote me this morning and said, “Ron, I am trying to sell this new idea of a sport consulting firm in Africa to get athletes linked up with universities, to get sponsors linked up with African sports.” He said, “I’ve got to make a presentation. Can you help me?” He sent me a presentation. Of course, he got a lot of red ink back on the computer because [I played devil’s advocate]. I said, “Please understand,” and he wrote back, “I do understand. This is exactly what I wanted.”

I was on a cruise and a friend said, “I have a family meeting on Sunday, and we’ve got to end the family partnership. There are no more funds and everyone’s going to be disappointed in me. How can I still have them embrace me but tell them we can’t do it any longer?” We went through the process and Monday morning came and he said, “Ron, it worked. The best part is I felt comfortable because I went through the process. Then I accomplished my goal.” That doesn’t always succeed, but most of the time it does, and that’s why it’s so important.

I’m never the smartest guy in the room, but I’m going to be the best prepared guy in the room.

Grant: In your experience, how important is it to have a coach working with you? Obviously, for the devil’s advocate part, it is critical. But when you do the drafting, when you do the delivering, can it just be an internal group? Do you need external advice?

Shapiro: I don’t think you necessarily need external advice. Most people aren’t going to go out and pay the hourly rates for external advice unless they have a softy like me who’s a friend, and they can give it me, and say, “Will you help me?” The bottom line is you can do it internally. I will turn to Cathi Shapiro, my beloved wife, and I will say, “Cathi, look I’ve got to make this presentation tomorrow morning. What do you think of it?” She is spiritual. She is not a business person. But she will look at it, and she’s detached enough to be able to give me ideas to take it to the next level. Then I’ll say, “Well, listen how I say it.” She’ll say, “Not falling the way it should.” She can guide me. If you can afford external help, great, but I think you can do this with internal teams….

Grant: How do you know when you’re ready? How many rounds of practice do you go through?

Shapiro: Well, one of the things I’ve learned in life — particularly when we have so much on our plate in our busy lives — is that I do quick timelines for things and then I just cut it off. If I go through drafting, if my devil’s advocate takes it apart and I practice it and get comfortable and try it out with someone, that’s probably it. It’s not going to be four times or five times because I’ve got to go on to the next thing. If it’s a major transaction with consequences for humanity or other people or for the bottom line of my company in a very material way, I may take it further. But generally, the Three Ds is intended to be a simple process so that you don’t feel it’s absorbing all of your time. But what’s the alternative? The alternative is to wing it. That’s when you come back to, “Why did I say that?”

Grant: Oftentimes, those errors are visible as soon as people started drafting?

Shapiro: When people get it down on paper, they start putting all the wrong things as well as a lot of the right things. The best devil’s advocate is able to help push the wrong things aside and focus on the right things, including how to articulate the right things. Perfecting Your Pitch: How to Find the Words to Succeed in Business and Life is not only about finding words but how to say them. I always say, “It’s not only what you say; it’s how you say it.” Because as a negotiator, you want the other side to feel your confidence. You want the other side to also feel that maybe it should go in that direction. That’s why the practicing and having the right people guide you can be so important.

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